PL51854B1 - - Google Patents
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- Publication number
- PL51854B1 PL51854B1 PL104665A PL10466564A PL51854B1 PL 51854 B1 PL51854 B1 PL 51854B1 PL 104665 A PL104665 A PL 104665A PL 10466564 A PL10466564 A PL 10466564A PL 51854 B1 PL51854 B1 PL 51854B1
- Authority
- PL
- Poland
- Prior art keywords
- nitro
- mixture
- chloroacridine
- minutes
- ether
- Prior art date
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 230000005712 crystallization Effects 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- JOUFIQVFVDNYRT-UHFFFAOYSA-N 9-chloro-1-nitroacridine Chemical compound C1=CC=C2C(Cl)=C3C([N+](=O)[O-])=CC=CC3=NC2=C1 JOUFIQVFVDNYRT-UHFFFAOYSA-N 0.000 claims description 3
- WYSFRKRTNWKBCD-UHFFFAOYSA-N 9-chloro-3-nitroacridine Chemical class C1=CC=CC2=NC3=CC([N+](=O)[O-])=CC=C3C(Cl)=C21 WYSFRKRTNWKBCD-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000000259 anti-tumor Effects 0.000 claims 1
- ZYZWOSIRFVIBRH-UHFFFAOYSA-N chloroform;cyclohexane Chemical compound ClC(Cl)Cl.C1CCCCC1 ZYZWOSIRFVIBRH-UHFFFAOYSA-N 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000012010 growth Effects 0.000 description 4
- 229910019213 POCl3 Inorganic materials 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- KVHISFJMQMSZHQ-UHFFFAOYSA-N acridin-10-ium;chloride;hydrochloride Chemical compound Cl.[Cl-].C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 KVHISFJMQMSZHQ-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 1-nitro-9 Chemical class 0.000 description 1
- NBJRFLIUYUFOIR-UHFFFAOYSA-N 2-(3-nitroanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC([N+]([O-])=O)=C1 NBJRFLIUYUFOIR-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N Dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- YMVWGSQGCWCDGW-UHFFFAOYSA-N N',N'-dimethyl-N-(1-nitroacridin-9-yl)propane-1,3-diamine Chemical compound C1=CC([N+]([O-])=O)=C2C(NCCCN(C)C)=C(C=CC=C3)C3=NC2=C1 YMVWGSQGCWCDGW-UHFFFAOYSA-N 0.000 description 1
- 241001272996 Polyphylla fullo Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940027998 antiseptics and disinfectants Acridine derivatives Drugs 0.000 description 1
- 201000009030 carcinoma Diseases 0.000 description 1
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000853 cresyl group Chemical class C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000017095 negative regulation of cell growth Effects 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001519 tissues Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965ST023858 DE1620473C3 (de) | 1964-05-25 | 1965-05-20 | Verfahren zur Herstellung von 1 -Nitro-9-(3'-dimethylaminopropylamino)-acridin-dihydrochlorid |
| SE670165A SE323373B (xx) | 1964-05-25 | 1965-05-21 | |
| FR18180A FR1458183A (fr) | 1964-05-25 | 1965-05-24 | Procédé de préparation de 1-nitro-9(dialcoylaminoalcoylamino) acridines |
| GB2210965A GB1093847A (en) | 1964-05-25 | 1965-05-25 | 1-nitro-9-[ªÏ-(dialkylamino)-alkylamino]-acridines |
| CH727465A CH440280A (de) | 1964-05-25 | 1965-05-25 | Verfahren zur Herstellung von 1-Nitro-9-(dialkylaminoalkylamino)-acridinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL51854B1 true PL51854B1 (xx) | 1966-06-25 |
Family
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